.ALPHA.-LAPACHONE

Details

Stereochemistry	ACHIRAL
Molecular Formula	C15H14O3
Molecular Weight	242.2699
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CC1(C)CCC2=C(O1)C(=O)C3=C(C=CC=C3)C2=O

InChI

InChIKey=PJWHOPKRRBUSDH-UHFFFAOYSA-N

InChI=1S/C15H14O3/c1-15(2)8-7-11-12(16)9-5-3-4-6-10(9)13(17)14(11)18-15/h3-6H,7-8H2,1-2H3

HIDE SMILES / InChI

Molecular Formula	C15H14O3
Molecular Weight	242.2699
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/19924086 | https://www.ncbi.nlm.nih.gov/pubmed/11008131 | https://www.ncbi.nlm.nih.gov/pubmed/24530030 | https://www.ncbi.nlm.nih.gov/pubmed/11501791

The bioactive quinone Alpha-lapachone was originally isolated from the heartwood of trees of the Bignoniaceae family (Tabebuia sp). It can also be found in other families such as Verbenaceae, Proteaceae, Leguminosae, Sapotaceae, Scrophulariaceae, and Malvaceae. Alpha-Lapachone showed potent cytotoxicity against different cancer cell lines. Alpha-lapachone is an "irreversible" inhibitor of topoisomerase II. Alpha-lapachone demonstrated antibacterial activity against pathogenic organisms Staphylococcus aureus and Salmonella typhi and antifungal activity against Candida albicans and Trichophyton mentagrophytes.

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Cystathionine gamma-synthase 1 Target ID: Q1M0P5 Gene ID: NA Gene Symbol: metB Target Organism: Helicobacter pylori (Campylobacter pylori) Sources: https://www.ncbi.nlm.nih.gov/pubmed/17981822	Inhibitor 8297		11.0 µM [IC50]
DNA topoisomerase II 66 Target ID: CHEMBL2094255 Sources: https://www.ncbi.nlm.nih.gov/pubmed/11320661 \| https://www.ncbi.nlm.nih.gov/pubmed/11008131	Inhibitor 8297

Conditions

Condition	Modality	Targets	Highest Phase	Product
Wound infection 4 Sources: https://www.ncbi.nlm.nih.gov/pubmed/16553949	Curative		Preclinical	Unknown Approved Use Unknown
Cancer 592 Sources: https://www.ncbi.nlm.nih.gov/pubmed/24530030	Primary		Basic research	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
Effects of beta-lapachone, a peroxide-generating quinone, on macromolecule synthesis and degradation in Trypanosoma cruzi.	1985 Jul	2409922
Novel mechanisms of DNA topoisomerase II inhibition by pyranonaphthoquinone derivatives-eleutherin, alpha lapachone, and beta lapachone.	2000 Nov 1	11008131
Novel mechanism of cellular DNA topoisomerase II inhibition by the pyranonaphthoquinone derivatives alpha-lapachone and beta-lapachone.	2001 Mar	11320661
Radermachera xylocarpa: the highly efficient source of lapachol and synthesis of its derivatives.	2001 Mar-Apr	11501791
Activity of natural and synthetic naphthoquinones against Toxoplasma gondii, in vitro and in murine models of infection.	2002 Sep	12375370
Inhibitory effects of lapachol derivatives on epstein-barr virus activation.	2003 Feb 20	12538012
Tabebuia avellanedae naphthoquinones: activity against methicillin-resistant staphylococcal strains, cytotoxic activity and in vivo dermal irritability analysis.	2006 Mar 22	16553949
Enzymatic characterization and inhibitor discovery of a new cystathionine {gamma}-synthase from Helicobacter pylori.	2008 Jan	17981822
The trypanocidal activity of naphthoquinones: a review.	2009 Nov 10	19924086
1,2,3-triazole-, arylamino- and thio-substituted 1,4-naphthoquinones: potent antitumor activity, electrochemical aspects, and bioisosteric replacement of C-ring-modified lapachones.	2014 Mar 1	24530030

Patents

Sample Use Guides

In Vivo Use Guide

Unknown

Route of Administration: Unknown

In Vitro Use Guide

1 uM alpha-lapachone failed to inhibit Trypanosoma cruzi epimastigotes DNA synthesis or the parasite growth in vitro, which suggests that inhibition of DNA synthesis was essential for beta-lapachone action on cell division and growth.

Substance Class	Chemical Created by `admin` on `Sat Dec 16 08:02:15 GMT 2023` Edited by `admin` on `Sat Dec 16 08:02:15 GMT 2023`
Record UNII	VPE3AOX9QV
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

.ALPHA.-LAPACHONE

Common Name

English

NSC-629747

Code

English

NSC-26327

Code

English

2H-NAPHTHO(2,3-B)PYRAN-5,10-DIONE, 3,4-DIHYDRO-2,2-DIMETHYL-

Systematic Name

English

ALPHA-LAPACHONE

Common Name

English

Code System Code Type Description

NSC

629747